Years before Dermot Mulroney filed for divorce from Prima Apollinaare in June 2025, the actor navigated another litigated split with his first wife, Catherine Keener.
Mulroney and Keener were married from 1990 to 2007. Like him, Keener is a prominent actress with credits in several notable films and television series like An American Crime and The 40-Year-Old Virgin. After their split, she continued to make her presence known in various A-list Hollywood projects, including Percy Jackson & the Olympians: The Lightning Thief and Begin Again.
The actor moved on with Apollinaare, who he married in 2010, but their marriage didn’t work out after Mulroney filed for divorce. In court documents reviewed by Us Weekly, Mulroney asked the court to award him spousal support while denying Apollinaare the ability to receive the same.
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Us Weekly looks back at the actor’s marriage history and divorces.
Dermot Mulroney Said He and Ex Prima Were ‘Stealth Hollywood Couple’
Catherine Keener
Mulroney and Keener met while working together on the 1989 film Survival Quest, multiple outlets reported. They walked down the aisle the following year.
Keener has built an impressive Hollywood resume. She made her acting debut in 1986’s About Last Night. In her early career, Keener also appeared in the television series Ohara, as well as episodes of Knightwatch, an episode of Seinfeld and the film Johnny Suede.
She earned an Academy Award nomination for Best Supporting Actress for her role of Maxine Lund in 1999’s Being John Malkovich. That year, she and Mulroney welcomed their son, Clyde.
Her second Oscars nomination in the category came after portraying Nelle Harper Lee in 2005’s Capote. That same year, Keener played the breakout role of Steve Carell’s love interest, Trish Piedmont, in The 40-Year-Old Virgin.
Mulroney and Keener separated in 2005. They were officially divorced in 2007.
“There are irreconcilable differences between the parties that have led to the irredeemable breakdown of the marriage, and there is no possibility of saving the marriage, through counseling or other means,” court documents obtained by Extra read.
After her marriage to Mulroney came to an end, Keener earned a Golden Globe nomination in 2008 for Best Actress in a Miniseries or Television Film for the role of Gertrude Baniszewski in An American Crime. She also notably appeared in 2017’s Get Out, the TV series Kidding from 2018 to 2020 and the film Joker: Folie à Deux in 2024.
Prima Apollinaare
Mulroney married his second wife in December 2010. They welcomed two children together, daughters Mabel and Sally.
Apollinaare is a musician, having released the album 22 in 2024. She appeared on the game show We Are Family in February 2024, where she performed a duet with Mulroney.
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They both reflected on the experience of performing together on the TV program.
“It was such an amazing phone call to get that the show reached out to us,” Mulroney told Entertainment Weekly in February 2024. “They knew Prima’s music and put together that we are this sort of secret couple even though we’ve been together for 20 years. Kind of a stealth Hollywood couple. So it really works perfectly for this show. And then it was such an honor to be on a game show that helps other people and isn’t just fun and games, although we could not have had more fun.”
Apollinaare echoed Mulroney’s sentiment, saying, “We had so much fun. I wish we could do it again.”
More than a year after the joint TV appearance, Mulroney filed for divorce from the singer in June 2025 after 14 years of marriage. He cited “irreconcilable differences” as the reason for their split. He asked the court for spousal support from Apollinaare, as well as requesting she be denied from receiving the same from him.
Us Weekly
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